A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid

doi:10.1007/s40242-014-4300-y

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (6): 915-918.doi: 10.1007/s40242-014-4300-y

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A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid

ZHAO Ying, MA Haiping, FU Zhijing, ZHANG Guoyan

College of Chemistry, Jilin University, Changchun 130012, P. R. China

Received:2014-08-07 Revised:2014-09-05 Online:2014-12-01 Published:2014-09-15
Contact: ZHANG Guoyan E-mail:guoyan@jlu.edu.cn
Supported by:
Supported by the Graduate Training Program Foundation of Jilin University, China.

Abstract

Abstract:

(S)-3-Hydroxy-3-phenylpropanoic acid is a potential progenitor of optically pure tomoxetine hydrochloride and fluoxetine hydrochloride which are currently available antidepressant drugs. We report here the chemical synthesis of racemic substrate (R,S)-ethyl 3-hydroxy-3-phenylpropanoate and enzymatic preparation of S-isomer of the substrate by employing Porcine pancreas lipase(PPL) as a biocatalyst. Optimum enzyme-catalyzed reaction conditions, such as the effects of the temperature, pH and solvents on conversion degree and enantiomeric excess, were studied. An optimal temperature of 35 ℃ and pH=7.5 are the best for the resolution of (R,S)-ethyl 3-hydroxy-3- pheylpropanoate by PPL when 0.1 mol/L phosphate buffer solution acts as a medium. This work provides a practically chemo-enzymatic preparation of chiral β-hydroxy acid by PPL.

Key words: Optically active β-hydroxy acid, Porcine pancreas lipase(PPL), Chemo-enzymatic process

ZHAO Ying, MA Haiping, FU Zhijing, ZHANG Guoyan. A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid[J]. Chemical Research in Chinese Universities, 2014, 30(6): 915-918.

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A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid

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